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Sorry, I thought I replied to you about this last week but it seems my reply vanished.

As far as I know Arduino Yun is the easiest option for wireless uploading.

It may be possible to hack something together using an ESP8266 module like the ESP-01, using something like our ESP-01 Shield as an adapter. However I don't know of any simple published solution to do this, you'd have to figure it out yourself.

If you want something running quickly and easily, probably best to go with Yun for now.

Yes yun is quite expensive still atm.
And I dont understand the type of coding needed to comunicate with such modules.

It would be great to see freetronics to be the first the have a low cost plug and play wireless uploading shield or module.
This would be great for the DMD display as most displays are out of reach if permanently mounted.
Plus tweaking of code is possible if your Arduino board is hard to get at a needs some disassembly to reload like my message matrix clocks.

If you are still looking around at playing with WiFi uploading capable Arduino's, then take a look at the Spark team's....or Particle now rather..... Photon range of devices. They are cloud based, so once you take 'ownership' of the device, your modules connect to the particle cloud, and can send/receive data (sensors etc), plus you can program in any web browser and upload the code to your device.